3) Chicago Bulls trades with the Pacers for Oladipo
If the Bulls are willing to take more of a win now approach to build up the roster this offseason, then a potential trade that could establish a foundation in talks between them and the Pacers could involve multiple moving parts. In this particular trade package, the Bulls must be willing to part ways with a key part of their young core along with future draft capital.
The Bulls part ways with the likes of 25-year-old shooting guard Zach LaVine, overpaid veteran small forward Otto Porter Jr., a future lottery protected first round draft pick, and their 2020 second round draft pick. In return, the Bulls would get Oladipo, stretch big man Myles Turner, and shooting guard/wing Jeremy Lamb, from the Pacers.
At this point, LaVine might be a more effective scorer to start in the backcourt for the Pacers than Oladipo would be. While Oladipo is a two-time NBA All-Star selection, his game fell off since he returned from that nasty quad tear that he suffered back in the midst of the 2018-19 season. LaVine meanwhile looks to be on a firm ascent to stardom.
But where the Bulls could really benefit from this trade package is adding wing depth in the form of Lamb while expanding their cap flexibility by offloading OPJ. They would have to get creative in free agency, or in the NBA Draft, to fill the additional need remaining on the wing. But they would have a ton of cap room freed up while getting a very nice addition to the frontcourt with Turner.